Structural Formula Vector Image
Title: Nafcillin
CAS Registry Number: 147-52-4
CAS Name: (2S,5R,6R)-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: 6-(2-ethoxy-1-naphthamido)penicillin
Molecular Formula: C21H22N2O5S
Molecular Weight: 414.47
Percent Composition: C 60.85%, H 5.35%, N 6.76%, O 19.30%, S 7.74%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn: F. P. Doyle et al., GB 880400; F. P. Doyle, J. H. C. Nayler, US 3157639 (1961, 1964 both to Beecham). Prepn of crystalline monohydrate: D. Flitter et al., US 3506645 (1970 to American Home Prod.). HPLC determn: P. Fan-Havard, M. C. Nahata, Ther. Drug Monit. 11, 105 (1989). Antibacterial activity: J. M. Steckelberg et al., Antimicrob. Agents Chemother. 37, 554 (1993). Clinical efficacy: D. L. Palmer et al., Ann. Thorac. Surg. 59, 626 (1995).
Derivative Type: Sodium salt monohydrate
CAS Registry Number: 7177-50-6; 985-16-0 (anhydrous)
Additional Names: Sodium 6-(2-ethoxy-1-naphthamido)penicillanate
Manufacturers' Codes: Wy-3277
Trademarks: Nafcil (Apothecon); Nallpen (SKB); Unipen (Wyeth-Ayerst)
Molecular Formula: C21H21N2NaO5S.H2O
Molecular Weight: 454.47
Percent Composition: C 55.50%, H 5.10%, N 6.16%, Na 5.06%, O 21.12%, S 7.06%
Properties: Sol in water. Insol in acetone, chloroform.
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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